Six Years of Boss Barista

February 1st marked the sixth anniversary of Boss Barista. Here's an incomplete list of lessons I've learned along the way.

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The very first episode of Boss Barista aired on February 1st, 2017. We'd been dragging the release date for weeks. Back then, I had a cohost named Jasper, and I remember we decided to pick a date—any date—as the absolute deadline for us to drop our first episode. Without that deadline, we would have spent weeks planning and imagining endless possibilities without recording a single episode. 

This story is past due: I thought about writing a piece commemorating the Boss Barista's sixth birthday, but then that date came and went. I didn't have time to think through the evolution of this show (and newsletter, which I started writing in 2019). When I think back, I still cringe at the mistakes I've made—I remember we recorded our first few episodes without mic stands and got yelled at for moving our hands too often as we held our microphones. 

But I've also learned a lot making this show. Boss Barista started as a feminist response to the world of coffee bros. The entire thing—the podcast, the newsletter, the silly memes and graphics I occasionally post on social media—is so different from when we began. 

One: To tell universal stories, get closer

When Boss Barista started, I thought I had to be everything to everyone. I covered topics I knew very little about and probably assumed more knowledge and expertise than I had any right to give. 

Right around when I launched the newsletter, I began to shift my perspective. The first article I wrote for this newsletter was about being "unemployable," a term I borrowed from a friend I was certain only a handful of people could connect to. But when I published the story, I was flabbergasted by how many people could relate—even a few days ago, someone shared this story on Twitter. It's one of my most shared and liked pieces. 

I try to only write about topics I care about and trust that the ideas and questions I find interesting will resonate with others. That doesn't mean every essay or podcast episode hits (I recently published a story on democratic lotteries that I found fascinating but didn't perform as well as past essays), but the ones that do seem to strike a chord I didn't know existed in others. Being more personable in my writing has helped me connect more with people. I am genuinely in conversation with listeners and readers rather than just throwing random things into the world and trying to cover as much ground as possible. 

Two: Figure out how you work

In 2021, I committed to producing Boss Barista regularly. At the time, I was releasing podcast episodes once a week maybe, and writing articles on the newsletter haphazardly. I'd publish a few articles a month and then go months without posting anything. 

I realize I thrive in structure after completing a 30-day yoga challenge on YouTube. I delighted in crossing out the days on a calendar, noting I had done my yoga on the designated day. I wondered if I could bring that structure into my writing. 

Now, I publish a podcast episode every other week instead of every week (I added full transcriptions into the mix in 2021, which was worth the tradeoff of slowing down podcast publication, and I now use an app called Descript to edit more carefully, another positive tradeoff). Every Thursday, I publish an article: on weeks I release a podcast interview, the article usually highlights a theme or idea that came up in the episode, and on off weeks, I'll write a long-form piece on a topic of my choosing. 

I abide by this schedule about 90% of the time, a level of consistency I've never had in my writing world. However, this structure might not work for you, so try to decipher your work style and habits that have proven effective. I also work from a standing desk and have a walking treadmill that helps me stay focused on the task in front of me (I tend to need a secondary action to help me stay on target). 

Three: Boss Barista is an ok name—or a lesson on decision-making

Maybe this isn't a lesson, but I've really struggled with the name "Boss Barista." It doesn't quite encapsulate what this newsletter and platform have evolved to be, which is wild because it felt perfect when Jasper and I first came up with it. From a phonetic standpoint, I loved that it was alliterative and used repetitive b's, a letter that felt less common. I liked the idea of calling the show "BB" for short. 

But there was more to the name: we picked it to signify the dozens of times a customer would turn to my cis-men colleagues and ask them technical coffee questions. I once pulled a shot for a customer, and he thanked my male co-worker for how good the shot tasted. I'd heard stories from my friends who would have pushy customers ask for the manager, expecting some white, cishet dude to appear from the shadows, only to tell the customer: "Actually, I'm the boss." 

That's the energy we were trying to generate with the title. Now that Boss Barista is more focused on collective action and equity in the workplace, the word "boss" feels icky sometimes, and I genuinely thought about changing it for a long time. Some folks also reported that the word "barista" made them think the show was just for baristas and not about coffee at large. 

But the name's the name! People have known this silly podcast and newsletter by Boss Barista for a long time, and I've learned that it's ok to let certain decisions lie.

Not everything needs to be perfect. I only have so much brain space to devote to making decisions, and I've learned to deduce what decisions are worth being thoughtful and measured—and which need to be made so we can keep moving. There may come a time when I sit down and think more about the name of the podcast, but the bigger lesson here is that not every decision matters as much as I might think.

Four: Ask simple questions

I still struggle with this, but before I transitioned to full-time freelancing work, I was a podcast editor for a beer website and used audio transcriptions to edit others' interviews. I don't think I acutally did this because it seemed too mean, but I remember transcribing an interview with one host who asked very long-winded questions. I wanted to send him snippets of the transcript that included just his questions—about as long as this paragraph—to demonstrate how difficult they were to follow. 

The simpler the question, the more room people have to explore, talk, and stumble on ideas that might be more interesting than the dumb questions I wrote down before I started the interview. Simplifying my questions slowed down interviews and helped me follow my guests more. When in doubt, asking people to elaborate more is always ok.  

I learned about asking simple and concrete questions from the book "Out on the Wire," which primarily focuses on podcast reporting, but I recommend it for anyone interviewing people. The author, Jessica Abel, is great and often discusses generating creative ideas. 

Five: Connect ideas

In college, I took a class called The Little Red Schoolhouse. The course was about academic writing, and as I write and edit more, I see lessons from my time in this class pop up. 

The most important lesson I learned in this class was to write effectively, your audience must be able to follow where you're going. To help readers stay in the same lane as you, the class taught us to make sure every sentence logically follows the preceding sentence. We'd break into small groups, and together, we'd do an exercise where a colleague would read a sentence from an article, and the rest of the group would try to guess what we expected the following sentence to be.

Our brains jump around and assume knowledge all the time, and I noticed that came out in my writing—I'd make inferences that seemed evident to me but weren't obvious to the reader. Focusing on connecting ideas forced me to slow down and consider every word I wrote, how a reader would move through a piece, and what information they needed to comprehend an idea or concept I wanted to explore. 

I learned so much in that one course, and I still refer to YouTube clips from previous lectures to improve and refine my writing. I'm lucky: I have an editor that goes over my pieces and does a lot more heavy lifting than might be obvious, but the lessons I learned from The Little Red Schoolhouse course have helped me zoom out, focus on precisely what I want to say, and make sure there's a pathway for readers to follow. 

Six: I am creative, and you are too

As a kid, I lamented that I couldn't draw as well as my friends. I wasn't a voracious writer, nor could I tell imaginative stories with interesting characters. I was also a terrible dancer: I took one ballet class when I was five, and the teacher gave out gold star stickers to signify how well we'd done in class. Everyone else in the class got five gold stars—I got four. I never went back. 

For years, I assumed I was not creative at all, and it was when I began podcasting and writing regularly I began to see the creativity within me. I think we sometimes speak about creativity very rigidly—at least, that's how I understood it—that it never occurred to me that everyone is creative, even me! 

I needed to realize my inherent creativity because it allowed me to trust my instincts more. It also gave me confidence—I could rely on myself and had everything within me to create and make cool stuff. I hope everyone reading this knows how creative they are. 

I have much more to learn, and I'm glad you're all with me on this journey. Thanks for six years of Boss Barista. 

Photo by Kalis Munggaran